16 Apr 2016
Hotel meet with crossdresser part 1
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We had been chatting online for sometime about our fantasies and had finally taken the plunge and decided to meet in person. We decided on a neutral location that would hopefully allow us both to be comfortable. We had both booked separate hotel rooms to allow us to be more discrete. I arrived around 4pm after travelling to London earlier that day for work. I checked in and made my way to my room.
The nerves were already beginning to get to me. This was a fantasy I have wanted to turn a reality for a long time. I'd never been with a guy before and being with a crossdresser seemed on the one hand slightly less gay than shagging a guy, but on the other extremely erotic! I still had 4 hours to kill before our scheduled meeting time. How was I going to keep my nerves at bay for the next 4 hours?
I opened my hotel room door and locked it behind me. What was I doing? I was praying the guy I would be meeting would be normal and live up to my expectations from our various online encounters. I immediately became hard from the excitement of what I was hopefully going to experience that evening! I went into the bathroom and undid my belt and flies and allowed my jeans to fall down to my ankles. I slipped my hand into my boxer shorts and grabbed my hard cock and began tugging to relieve some sexual tension. After a minute of two I had to stop to avoid coming and spoiling the rest of evening!
I sat down on the end of the bed and removed my jeans and boxer shorts. Then laid back half naked, my naked cock twitching from excitement. I grabbed the remote and turned on the tv in search of some porn. I managed to find a MILF movie which kept me entertained for sometime. Masturbating and feeling my prostate bringing me almost to climax numerous times. I just hoped my cd date this evening would be as slutty as the amateur milf on the tv. My excitement was building, so it was time to check if my slut had arrived at the hotel. I sent a text to ask if he had arrived and which room number he was in. After a long 15 minute wait I finally received a reply "Stuck in traffic, will be there in another 30mins honey!"
It was time to start massaging my ass to be ready for every eventuality. I looked through my bag for lube and made myself comfortable on the bed and positioned a pillow under my lower back to give me better access to my hole.
It was almost time for action, it was 19.50. I sent her a text to check she was ready. I got a reply almost immediately "yes honey, all dressed and horny. Come over when you're ready. Room 352 x.". I couldn't wait any longer so I tidied up my room and got ready to leave. I was on the second floor and her room was on the third. I took the lift upstairs and followed the signs to her room luckily it was at the end of a corridor so gave us some privacy. Arriving at her door, I knocked quietly, nervous as hell. The door unlocked and opened to reveal a beautiful figure. Tall, slim and with legs to die for. She was wearing a long black wig, a black blouse, pencil skirt, stockings and high heels. I stepped inside the room and stepped close to her. We were both as nervous as hell. She whispered "hello darling" in my ear as we began fondling each other. My hands were immediately drawn to her tight ass and soon moved down to her pantyhosed thighs. She was groaning from all the attention with her back against the wall. I worked my hands slowly up her inner thighs until I reached her mound. Her cock was straining inside her tight thong. I worked my middle finger between her legs to locate her asshole and massaged the string of thong into her hole. She was groaning with pleasure as I worked my finger deeper and deeper into her ass. She was obviously prepared for me as her ass had been lubed in advance! I moved my attention to her cock and took it in the palm of my hand and massaged it until it sprug out the side of her thong. Holding onto the shaft I pumped a few times as she groaned with increasing excitement. By this point she was grasping at my hard cock through my jeans and struggling to open my fly buttons with one hand. Wanting to see her cock I dopped down onto my knees, lifted her skirt up to her waist and licked the length of her shaft, stopping to engulf the entire head in my mouth. The taste of precum was delightful. We both stopped playing to move further into the room where we both sat on the end of the bed.
Immediately our hands went for each others crotches. She unbuttened my flys and slipped her hands in to feel my hard cock through my boxer shorts. I began caressing her pantyhosed thighs and inner legs working my hands closer to her crotch. She pulled my boxers down and pulled my cock out. Her head lowered to engulf my cock. I said back on the bed and removed my trousers, her mouth firmly sucking my cock the whole time. She was kneeling next to me on the bed giving me head and I had my hands up her skirt feeling her cock and ass. I pulled her ass towards me to get into 69 position and she quickly got the message. She put one leg over me and gave me a lovely view of her ass, black thong, and hard cock hanging out. I lifted my head up to lick between her balls and ass hole. Teasing her hole with my tongue then sucking each ball in turn. Occassionally she would lift her ass to position her cock over my mouth which I couldn.t resist but suck along the shaft.
After a few minutes in this position things were getting pretty steamy. Time to make a move or the excitement might climax too quickly. I rolled her off me and onto the bed and she lay face down. I kneeled with my legs over her legs and lifted her skirt to reveal that ass. I pulled her thong down, stopping to massage her bum cheeks, then pulled them off completely.
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